Potassium Carbonate → 4-(1H-1,2,3-Triazol-1-yl)benzaldehyde

HRID 1941345Notes

Reaction equation

HRID 1941345 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1>N1C=CC=CC=1>[N:1]1([C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 178418936HCID 178418936, compound

Product 1

HCID 108449434-(1H-1,2,3-Triazol-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1,2,3-triazole (3.4 ml, 58.7 mmol), potassium carbonate (9.03 g, 65.4 mmol), and 4-fluorobenzaldehyde (6.3 ml, 58.7 mmol) in pyridine (30 ml) is heated under nitrogen atmosphere at reflux overnight. After pyridine is distilled, the mixture is diluted with methylene chloride, filtered and washed with chloroform. The combined filtrate is washed with water, dried over magnesium sulfate, and concentrated in vacuo. The crude material is purified by column chromatography on silica with hexane/ethyl acetate (5:1) to give 4-(1,2,3-triazol-1-yl)-benzaldehyde and with hexane/ethyl acetate (1:2) to give 4-(1,2,3-triazol-1-yl)-benzaldehyde.

Workup

  1. temperatureis heated under nitrogen atmosphere
  2. temperatureat reflux overnight
  3. distillationAfter pyridine is distilled
  4. additionthe mixture is diluted with methylene chloride
  5. filtrationfiltered
  6. washwashed with chloroform
  7. washThe combined filtrate is washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe crude material is purified by column chromatography on silica with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-0f1d01cdfcef45f8b18c38c57d1c2017
Source dataset
uspto-grants-1997_12
Patent number
US05703106

Reaction notes

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